CNRS, Institut de Chimie des Substances Naturelles, Université Paris-Saclay, F-91190 Gif-sur-Yvette, France.
IRD, CNRS, Ifremer, University Brest, LEMAR, F-29280 Plouzane, France.
Mar Drugs. 2022 Oct 11;20(10):635. doi: 10.3390/md20100635.
Naturally occurring epimeric hydroxy-polyene glycerol ether pericharaxins A () and B () were isolated from the calcarean sponge . The structural and stereochemical characterization of both diastereoisomers were established on the basis of spectroscopic data analysis and total synthesis in seven steps. The mixture of pericharaxins A () and B () was proven to be epimeric by chiral-phase HPLC analysis of both synthetic and natural samples. Further separation of the epimers and application of Mosher's method to the synthetic compounds allowed unequivocal absolute configuration assignment. While natural products and the synthetic intermediates were shown to be non-cytotoxic on the HCT116 cell line, the endochondral differentiation activity using human type X collagen transcription activity in ATDC5 cells is interesting.
天然存在的差向异构羟基聚烯甘油醚聚甲藻素 A()和 B()从钙质海绵中分离得到。基于光谱数据分析和七步全合成，确定了两种非对映异构体的结构和立体化学特征。通过对合成和天然样品的手性相高效液相色谱分析，证明了聚甲藻素 A()和 B()的混合物是差向异构体。进一步分离差向异构体，并应用莫舍尔法对合成化合物进行分析，可明确绝对构型的归属。虽然天然产物和合成中间体对 HCT116 细胞系没有细胞毒性，但在 ATDC5 细胞中使用人 X 型胶原蛋白转录活性的软骨内分化活性很有趣。
